Clopidol
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Clopidol
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CAS No:
2971-90-6
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Formula:
C7H7Cl2NO
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Chemical Name:
Clopidol
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Synonyms:
4-Pyridinol,3,5-dichloro-2,6-dimethyl-;3,5-Dichloro-2,6-dimethyl-4-pyridinol;Coyden;Meticlorpindol;Clopidol;Coyden 25;Coccidiostat C;2,6-Dimethyl-3,5-dichloro-4-pyridinol;Methylchlorpindol;3,5-Dichloro-4-hydroxy-2,6-dimethylpyridine;3,5-Dichloro-2,6-dimethylpyridinol;Methylchloropindol;Lerbek;3,5-Dichloro-2,6-dimethyl-4-hydroxypyridine;Pharmcoccid;Farmcoccid;WR 61112;NSC 253479;2,6-Dimethyl-3,5-dichloro-4-hydroxypyridine;Pharmcoccid 10;11116-46-4;68821-99-8
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CAS No:
Description
Clopidol is an organic compound that is used as in veterinary medicine, as a coccidiostat.
Clopidol is a white to light-brown, crystalline solid. Mp: 320°C. Practically insoluble in water. Administered to poultry to prevent the growth of pathogenic parasites.|White to light-brown, crystalline solid.
Clopidol is a white to light-brown, crystalline solid. Mp: 320°C. Practically insoluble in water. Administered to poultry to prevent the growth of pathogenic parasites.|A very effective anticoccidial agent used in poultry.
Clopidol Basic Attributes
192.04300
192.04
221-008-2
8J763HFF5N
758964|253479
DTXSID8041793
White to light-brown, crystalline solid|Powder
2933399090
Characteristics
32.86000
2.6
Clopidol is a white to light-brown, crystalline solid. Mp: 320°C. Practically insoluble in water. Administered to poultry to prevent the growth of pathogenic parasites.
1.41g/cm3
320 °C
219.7ºC at 760 mmHg
70.4ºC
1.578
H2O: Insoluble
0-6ºC
0.117mmHg at 25°C
LD50 orally in rats: 18 g/kg (Plisek)
Noncombustible Solid, but dust may explode in cloud form.
Noncombustible solid, but dust may explode in cloud form.
Henry's Law constant = 1.02X10-9 cu m-atm/mol at 25 °C (est)
pKa = 4.79 (est)
131.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Hydroxyl radical reaction rate constant = 4.09X10-12 cu cm/molec-sec at 25 °C (est)
No rapid reaction with air No rapid reaction with water
Amines, Phosphines, and Pyridines
CLOPIDOL is a non-combustible as a solid, but dust may burn rapidly or explode when mixed with air and ignited.
Noncombustible Solid, but dust may explode in cloud form.
Safety Information
NONH for all modes of transport
2
R36/37/38
S26
UU7711500
Xi
P261-P305 + P351 + P338
H315-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Tolerances for residues of clopidol (3,5-dichloro-2,6-dimethyl-4-pyridinol) in food are established as follows: In cereal grains, vegetables, and fruits.|Tolerances for residues of clopidol (3,5-dichloro-2,6-dimethyl-4-pyridinol) in food are established as follows: In chickens and turkeys: (1) in uncooked liver and kidney. (2) in uncooked muscle.|Tolerances for residues of clopidol (3,5-dichloro-2,6-dimethyl-4-pyridinol) in food are established as follows: In cattle, sheep, and goats: (1) in uncooked kidney. (2) in uncooked liver.|Tolerances for residues of clopidol (3,5-dichloro-2,6-dimethyl-4-pyridinol) in food are established as follows: In swine: in uncooked edible tissues.|For more FDA Requirements (Complete) data for Clopidol (7 total), please visit the HSDB record page.
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P403+P233, P405, and P501
Skin: No recommendation is made specifying the need for personal protective equipment for the body. Eyes: No recommendation is made specifying the need for eye protection. Wash skin: No recommendation is made specifying the need for washing the substance from the skin (either immediately or at the end of the work shift). Remove: No recommendation is made specifying the need for removing clothing that becomes wet or contaminated. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Safety glasses with side-shields conforming to EN166.|Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|(See protection codes)
Noncombustible solid, but dust may explode in cloud form.
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self contained breathing apparatus for fire fighting if necessary.
Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 15 mg/cu m (total dust); 5 mg/cu m (respirable fraction).
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 mg/cu m (total); 5 mg/cu m (resp)|15 Min Short-Term Exposure Limit: 20 mg/cu m (total)
Toxicity
LD50 Rat oral 18 g/kg /SRP: 18,000 mg/kg/
/AQUATIC SPECIES/ The short-term toxicity (EC50 respectively LC50 after 2 or 4 days) of 13 feed additives was determined to 4 freshwater organisms of different trophical levels: Chlorella pyrenoidosa, Daphnia magna, Lebistes reticulatus and Salmo gairdneri. The most toxic (LC(EC)50 less than 1 mg/L) were robenidine (to all tested organisms) and stenorol (to Daphnia); moderately toxic (1 less than LC(EC)50 less than 10 mg/L) was pyrimethamine. Amprolium, ethopabate, furazolidone and zoalene proved to be little toxic (LC(EC)50 greater than 10 mg/L); whereas buquinolate, carbadox, clopidol, decoquinate, grofas and sulfaquinoxaline were under the experimental conditions not toxic for the tested organisms.
Clopidol's production and use as a coccidiostat(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 660(SRC), determined from a structure estimation method(2), indicates that clopidol is expected to have low mobility in soil(SRC). Volatilization of clopidol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Clopidol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2011).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 660(SRC), determined from a water solubility of 10 mg/L(2) and a regression-derived equation(3), indicates that clopidol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.0X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 28(SRC), from an estimated log Kow(7) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), clopidol, which has an estimated vapor pressure of 1.2X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase clopidol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.9 days(SRC), calculated from its rate constant of 4.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase clopidol may be removed from the air by wet or dry deposition(SRC). Clopidol does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of clopidol with photochemically-produced hydroxyl radicals has been estimated as 4.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.9 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Clopidol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Clopidol does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 28 was calculated in fish for clopidol(SRC), using an estimated log Kow of 2.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).|A BCF of 0.0011 was measured in cattle after being exposed to clopidol at a dietary concentration of 500 ppm over 28 days; the concentration in beef fat tissue was 0.2-0.9 ppm(1).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of clopidol can be estimated to be 660(SRC). According to a classification scheme(2), this estimated Koc value suggests that clopidol is expected to have low mobility in soil.
The Henry's Law constant for clopidol is estimated as 1.0X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that clopidol is expected to be essentially nonvolatile from water surfaces(2). Clopidol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.2X10-6 mm Hg(SRC), determined from a fragment constant method(3).
Over a two-year period from April 1997 to July 1999, over 3500 samples of domestic and imported eggs in Canada were analyzed for a variety of veterinary drugs; out of 110 samples tested for clopidol, two samples from Maryland tested presumptive positive (but not confirmed positive)(1).
Occupational exposure to clopidol may occur through dermal contact with this compound at workplaces where clopidol is produced or used. Use data indicate that exposure to the general population will be limited. (SRC)
Drug Information
THERAPEUTIC CATEGORY (VETERINARY): Coccidiostat|Used as an anticoccidiostat in poultry.|Clopidol is mainly coccidiostatic and is active only against the sporozoite stage of Eimeria.|MEDICATION (VET): Turkeys grown for meat purposes only: As an aid in the prevention of leucocytozoonosis caused by Leucocytozoon smithi.|MEDICATION (VET): Broiler and replacement chickens: As an aid in the prevention of coccidiosis in broilers and replacements for caged layers caused by E. tenella, Eimeria necatrix, Eimeria Acervulina, Eimeria maxima, Eimeria brunetti, Eimeria mivati.
Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)
Exposure Routes: inhalation, skin and/or eye contact Symptoms: Irritation eyes, skin, nose, throat; cough Target Organs: Eyes, skin, respiratory system (NIOSH, 2016)
Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, wash the contaminated skin with soap and water. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. Other measures are usually unnecessary. (NIOSH, 2016)|(See procedures)
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
3,5-Dichloro-2,6-dimethyl-4-pyridinol
inhalation, skin and/or eye contact
irritation eyes, skin, nose, throat; cough
Eyes, skin, respiratory system
Clopidol Use and Manufacturing
In three 500 ml flask, 130 g of ethyl acetoacetate (1 mole), Styrene-DVB (D301T) 39 g resin, reaction at 30 5 hours, 100 ml of distilled water, stirring the ammonia released 85 g (5 mol), reacted at 10 deg.] C after 2 hours with stirring chlorine gas at 142 g (2 mol), reacted at 30 2 hours and filtered Styrene-DVB (D301 T) and the resin solid cake was washed with NaOH (10percent concentration) was washed with an aqueous solution of 100 ml, Styrene-DVB (D301T) resin is recyclable. The filtrate was distilled to remove a small amount of ethanol, allowed to stand to crystallize, filtered and dried to give the desired product 87.8 g, 91.5percent yield.
1. GABA Cl channel agonist, antiparasitic
2. An antibiotic used in veterinary medicine as a coccidiostat in poultry. Showed low order of acute and chronic toxicity in animals.
3. An antiprotozoal agent.
COYDEN 25%, Active drug ingredient: Clopidol 113.5 gm/lb (25%). Other ingredients: Rice Hulls, Mineral Oil, Fatty Acid Glycerides (Huvepharma, Inc)
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Computed Properties
Molecular Weight:192.04
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:190.9904692
Monoisotopic Mass:190.9904692
Topological Polar Surface Area:29.1
Heavy Atom Count:11
Complexity:252
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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